data_228 # _chem_comp.id 228 _chem_comp.name "N-[2-(1,3-BENZODIOXOL-5-YL)ETHYL]-1-[2-(1H-IMIDAZOL-1-YL)-6-METHYLPYRIMIDIN-4-YL]-D-PROLINAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H24 N6 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2007-02-14 _chem_comp.pdbx_modified_date 2011-06-04 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 420.464 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 228 _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details "OpenEye/OEToolkits V1.4.2" _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code ? _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site PDBJ # loop_ _chem_comp_atom.comp_id _chem_comp_atom.atom_id _chem_comp_atom.alt_atom_id _chem_comp_atom.type_symbol _chem_comp_atom.charge _chem_comp_atom.pdbx_align _chem_comp_atom.pdbx_aromatic_flag _chem_comp_atom.pdbx_leaving_atom_flag _chem_comp_atom.pdbx_stereo_config _chem_comp_atom.model_Cartn_x _chem_comp_atom.model_Cartn_y _chem_comp_atom.model_Cartn_z _chem_comp_atom.pdbx_model_Cartn_x_ideal _chem_comp_atom.pdbx_model_Cartn_y_ideal _chem_comp_atom.pdbx_model_Cartn_z_ideal _chem_comp_atom.pdbx_component_atom_id _chem_comp_atom.pdbx_component_comp_id _chem_comp_atom.pdbx_ordinal 228 C28 C28 C 0 1 Y N N 70.539 -4.547 50.720 -4.219 1.925 -0.800 C28 228 1 228 C27 C27 C 0 1 Y N N 69.674 -4.575 51.829 -5.385 2.114 -1.512 C27 228 2 228 O31 O31 O 0 1 N N N 68.558 -5.305 52.070 -6.614 2.358 -0.981 O31 228 3 228 C30 C30 C 0 1 N N N 67.958 -4.745 53.246 -7.415 2.463 -2.176 C30 228 4 228 O29 O29 O 0 1 N N N 68.966 -3.946 53.874 -6.656 2.281 -3.390 O29 228 5 228 C26 C26 C 0 1 Y N N 69.941 -3.764 52.944 -5.409 2.071 -2.888 C26 228 6 228 C25 C25 C 0 1 Y N N 71.076 -2.933 52.947 -4.268 1.835 -3.627 C25 228 7 228 C24 C24 C 0 1 Y N N 71.938 -2.908 51.839 -3.073 1.641 -2.930 C24 228 8 228 C23 C23 C 0 1 Y N N 71.668 -3.714 50.722 -3.063 1.687 -1.533 C23 228 9 228 C22 C22 C 0 1 N N N 72.573 -3.641 49.486 -1.760 1.474 -0.802 C22 228 10 228 C21 C21 C 0 1 N N N 73.919 -4.347 49.705 -1.499 0.007 -0.466 C21 228 11 228 N20 N20 N 0 1 N N N 73.732 -5.806 49.817 -0.262 -0.185 0.257 N20 228 12 228 C18 C18 C 0 1 N N N 74.008 -6.637 48.805 0.949 -0.415 -0.367 C18 228 13 228 O19 O19 O 0 1 N N N 74.425 -6.274 47.705 1.144 -0.486 -1.575 O19 228 14 228 C17 C17 C 0 1 N N R 73.764 -8.128 49.088 2.099 -0.582 0.577 C17 228 15 228 C16 C16 C 0 1 N N N 75.025 -8.717 49.729 2.302 -2.062 0.910 C16 228 16 228 C15 C15 C 0 1 N N N 74.444 -9.809 50.606 3.240 -2.549 -0.184 C15 228 17 228 C14 C14 C 0 1 N N N 73.312 -9.044 51.280 4.168 -1.358 -0.409 C14 228 18 228 N13 N13 N 0 1 N N N 72.708 -8.357 50.119 3.344 -0.193 -0.086 N13 228 19 228 C1 C1 C 0 1 Y N N 71.377 -8.180 49.978 3.773 1.109 -0.254 C1 228 20 228 N1 N1 N 0 1 Y N N 70.583 -8.446 51.033 2.955 2.167 0.066 N1 228 21 228 C6 C6 C 0 1 Y N N 70.790 -7.740 48.774 5.062 1.348 -0.759 C6 228 22 228 C5 C5 C 0 1 Y N N 69.397 -7.598 48.727 5.454 2.662 -0.913 C5 228 23 228 C12 C12 C 0 1 N N N 68.710 -7.092 47.461 6.815 2.965 -1.445 C12 228 24 228 N4 N4 N 0 1 Y N N 68.654 -7.884 49.816 4.672 3.718 -0.608 N4 228 25 228 C3 C3 C 0 1 Y N N 69.240 -8.304 50.963 3.453 3.403 -0.130 C3 228 26 228 N7 N7 N 0 1 Y N N 68.511 -8.530 52.051 2.621 4.466 0.196 N7 228 27 228 C8 C8 C 0 1 Y N N 67.184 -8.462 52.149 1.350 4.379 0.694 C8 228 28 228 C9 C9 C 0 1 Y N N 66.856 -8.765 53.398 0.941 5.682 0.854 C9 228 29 228 NFE NFE N 0 1 Y N N 67.981 -9.019 54.073 1.924 6.560 0.469 NFE 228 30 228 C11 C11 C 0 1 Y N N 68.994 -8.878 53.237 2.921 5.797 0.079 C11 228 31 228 H28 H28 H 0 1 N N N 70.333 -5.170 49.862 -4.213 1.962 0.284 H28 228 32 228 H301 1H30 H 0 0 N N N 67.088 -4.127 52.978 -7.881 3.454 -2.200 H301 228 33 228 H302 2H30 H 0 0 N N N 67.599 -5.534 53.923 -8.204 1.703 -2.139 H302 228 34 228 H25 H25 H 0 1 N N N 71.285 -2.312 53.805 -4.291 1.801 -4.710 H25 228 35 228 H24 H24 H 0 1 N N N 72.809 -2.269 51.846 -2.158 1.453 -3.486 H24 228 36 228 H221 1H22 H 0 0 N N N 72.767 -2.583 49.257 -1.780 2.060 0.125 H221 228 37 228 H222 2H22 H 0 0 N N N 72.056 -4.149 48.659 -0.931 1.878 -1.396 H222 228 38 228 H211 1H21 H 0 0 N N N 74.579 -4.134 48.851 -2.301 -0.377 0.173 H211 228 39 228 H212 2H21 H 0 0 N N N 74.366 -3.975 50.639 -1.455 -0.612 -1.368 H212 228 40 228 HN20 HN20 H 0 0 N N N 73.388 -6.186 50.676 -0.285 -0.149 1.271 HN20 228 41 228 H17 H17 H 0 1 N N N 73.478 -8.578 48.126 1.904 0.005 1.480 H17 228 42 228 H161 1H16 H 0 0 N N N 75.724 -9.116 48.979 1.371 -2.637 0.942 H161 228 43 228 H162 2H16 H 0 0 N N N 75.628 -7.980 50.280 2.798 -2.157 1.884 H162 228 44 228 H151 1H15 H 0 0 N N N 74.085 -10.672 50.026 3.785 -3.455 0.095 H151 228 45 228 H152 2H15 H 0 0 N N N 75.163 -10.268 51.301 2.673 -2.761 -1.099 H152 228 46 228 H141 1H14 H 0 0 N N N 73.677 -8.339 52.041 5.025 -1.405 0.271 H141 228 47 228 H142 2H14 H 0 0 N N N 72.612 -9.678 51.843 4.533 -1.328 -1.441 H142 228 48 228 H6 H6 H 0 1 N N N 71.399 -7.518 47.910 5.715 0.521 -1.013 H6 228 49 228 H121 1H12 H 0 0 N N N 67.633 -6.970 47.651 7.205 3.884 -0.992 H121 228 50 228 H122 2H12 H 0 0 N N N 69.143 -6.123 47.171 7.516 2.147 -1.234 H122 228 51 228 H123 3H12 H 0 0 N N N 68.859 -7.818 46.648 6.796 3.094 -2.535 H123 228 52 228 H8 H8 H 0 1 N N N 66.499 -8.206 51.354 0.860 3.434 0.887 H8 228 53 228 H9 H9 H 0 1 N N N 65.854 -8.800 53.800 -0.010 6.033 1.226 H9 228 54 228 H11 H11 H 0 1 N N N 70.037 -9.021 53.478 3.873 6.150 -0.295 H11 228 55 # loop_ _chem_comp_bond.comp_id _chem_comp_bond.atom_id_1 _chem_comp_bond.atom_id_2 _chem_comp_bond.value_order _chem_comp_bond.pdbx_aromatic_flag _chem_comp_bond.pdbx_stereo_config _chem_comp_bond.pdbx_ordinal 228 C28 C23 DOUB Y N 1 228 C28 C27 SING Y N 2 228 C28 H28 SING N N 3 228 C27 O31 SING N N 4 228 C27 C26 DOUB Y N 5 228 O31 C30 SING N N 6 228 C30 O29 SING N N 7 228 C30 H301 SING N N 8 228 C30 H302 SING N N 9 228 O29 C26 SING N N 10 228 C26 C25 SING Y N 11 228 C25 C24 DOUB Y N 12 228 C25 H25 SING N N 13 228 C24 C23 SING Y N 14 228 C24 H24 SING N N 15 228 C23 C22 SING N N 16 228 C22 C21 SING N N 17 228 C22 H221 SING N N 18 228 C22 H222 SING N N 19 228 C21 N20 SING N N 20 228 C21 H211 SING N N 21 228 C21 H212 SING N N 22 228 N20 C18 SING N N 23 228 N20 HN20 SING N N 24 228 C18 O19 DOUB N N 25 228 C18 C17 SING N N 26 228 C17 C16 SING N N 27 228 C17 N13 SING N N 28 228 C17 H17 SING N N 29 228 C16 C15 SING N N 30 228 C16 H161 SING N N 31 228 C16 H162 SING N N 32 228 C15 C14 SING N N 33 228 C15 H151 SING N N 34 228 C15 H152 SING N N 35 228 C14 N13 SING N N 36 228 C14 H141 SING N N 37 228 C14 H142 SING N N 38 228 N13 C1 SING N N 39 228 C1 C6 SING Y N 40 228 C1 N1 DOUB Y N 41 228 N1 C3 SING Y N 42 228 C6 C5 DOUB Y N 43 228 C6 H6 SING N N 44 228 C5 C12 SING N N 45 228 C5 N4 SING Y N 46 228 C12 H121 SING N N 47 228 C12 H122 SING N N 48 228 C12 H123 SING N N 49 228 N4 C3 DOUB Y N 50 228 C3 N7 SING Y N 51 228 N7 C8 SING Y N 52 228 N7 C11 SING Y N 53 228 C8 C9 DOUB Y N 54 228 C8 H8 SING N N 55 228 C9 NFE SING Y N 56 228 C9 H9 SING N N 57 228 NFE C11 DOUB Y N 58 228 C11 H11 SING N N 59 # loop_ _pdbx_chem_comp_descriptor.comp_id _pdbx_chem_comp_descriptor.type _pdbx_chem_comp_descriptor.program _pdbx_chem_comp_descriptor.program_version _pdbx_chem_comp_descriptor.descriptor 228 SMILES ACDLabs 10.04 "O=C(NCCc1ccc2OCOc2c1)C5N(c3nc(nc(c3)C)n4ccnc4)CCC5" 228 SMILES_CANONICAL CACTVS 3.341 "Cc1cc(nc(n1)n2ccnc2)N3CCC[C@@H]3C(=O)NCCc4ccc5OCOc5c4" 228 SMILES CACTVS 3.341 "Cc1cc(nc(n1)n2ccnc2)N3CCC[CH]3C(=O)NCCc4ccc5OCOc5c4" 228 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "Cc1cc(nc(n1)n2ccnc2)N3CCC[C@@H]3C(=O)NCCc4ccc5c(c4)OCO5" 228 SMILES "OpenEye OEToolkits" 1.5.0 "Cc1cc(nc(n1)n2ccnc2)N3CCCC3C(=O)NCCc4ccc5c(c4)OCO5" 228 InChI InChI 1.03 "InChI=1S/C22H24N6O3/c1-15-11-20(26-22(25-15)27-10-8-23-13-27)28-9-2-3-17(28)21(29)24-7-6-16-4-5-18-19(12-16)31-14-30-18/h4-5,8,10-13,17H,2-3,6-7,9,14H2,1H3,(H,24,29)/t17-/m1/s1" 228 InChIKey InChI 1.03 LBCGUKCXRVUULK-QGZVFWFLSA-N # loop_ _pdbx_chem_comp_identifier.comp_id _pdbx_chem_comp_identifier.type _pdbx_chem_comp_identifier.program _pdbx_chem_comp_identifier.program_version _pdbx_chem_comp_identifier.identifier 228 "SYSTEMATIC NAME" ACDLabs 10.04 "N-[2-(1,3-benzodioxol-5-yl)ethyl]-1-[2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl]-D-prolinamide" 228 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R)-N-[2-(1,3-benzodioxol-5-yl)ethyl]-1-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)pyrrolidine-2-carboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 228 "Create component" 2007-02-14 PDBJ 228 "Modify aromatic_flag" 2011-06-04 RCSB 228 "Modify descriptor" 2011-06-04 RCSB #